Composition for optical material

ABSTRACT

The present invention relates to a composition for optical materials, comprising (a) a compound having in one molecule at least one structure represented by the following Formula  1:   
                 
 
     wherein R 1  is a C 0-10  hydrocarbon group, each of R 2 , R 3  and R 4  is a C 1-10  hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5, and n is 0 to 5; (b) a compound having in one molecule at least one isocyanate group and/or at least one isothiocyanate group; (c) a compound having in one molecule at least one mercapto group; and (d) an inorganic compound having sulfur atom and/or selenium atom, and also relates to an optical material produced by polymerization curing the composition, a production method thereof, and an optical lens comprising the optical material. The present invention provides a high refractive, high Abbe&#39;s number optical material having an improved impact resistance.

TECHNICAL FIELD

[0001] The present invention relates to a composition suitable forproducing an optical material such as plastic lens, prism, opticalfiber, information recording medium, and filter, particularly, forproducing a plastic spectacle lens. The present invention furtherrelates to an optical material produced by polymerization curing thecomposition, a production method thereof, and an optical lens comprisingthe optical material.

BACKGROUND ART

[0002] Plastic materials are recently widely used in manufacturingoptical materials, particularly, spectacle lenses because of their lightweight, toughness and easiness of dyeing. Optical materials,particularly, spectacle lenses are required to have, in addition to alow specific gravity, a high refractive index and a large Abbe's numberfor optical properties, and a high heat resistance and a high impactresistance for physical properties. A large refractive index makes itpossible to reduce the thickness of lens. A high Abbe's number reducesthe chromatic aberration of lens. A high heat resistance and a highimpact strength facilitate the fabrication process and are important inview of safety in use.

[0003] The inventors found a novel sulfur compound capable of providinga thin optical material having a low chromatic aberration, and filedapplications for patent (Japanese Patent Application Laid-Open Nos.9-71580, 9-110979 and 9-255781, and Japanese Patent ApplicationNo.2000-20627). The inventors further found a resin composition capableof enhancing the impact resistance, and filed applications for patent(Japanese Patent Application Laid-Open Nos. 11-292950 and 11-318960).However, the refractive index decreased with increasing impactresistance, because the component for improving the impact resistance,in turn, reduces the refractive index. Therefore, the novel sulfurcompound, found by the inventors, capable of providing a thin opticalmaterial having a low chromatic aberration fails to exert its effectsufficiently in the resin composition having an improved impactresistance.

DISCLOSURE OF INVENTION

[0004] An object of the present invention is to provide a highrefractive, high Abbe's number optical material having a higher impactresistance.

[0005] The present invention provides a composition for opticalmaterials, comprising:

[0006] (a) a compound having in one molecule at least one structurerepresented by the following Formula 1:

[0007] wherein R¹ is a C₀₋₁₀ hydrocarbon group, each of R², R³ and R⁴ isa C₁₋₁₀ hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5,and n is 0 to 5;

[0008] (b) a compound having in one molecule at least one isocyanategroup and/or isothiocyanate group;

[0009] (c) a compound having in one molecule at least one mercaptogroup; and

[0010] (d) an inorganic compound having sulfur atom and/or seleniumatom.

[0011] The present invention further provides an optical materialproduced by polymerization curing the composition, a production methodthereof, and an optical lens comprising the optical material.

BEST MODE FOR CARRYING OUT THE INVENTION

[0012] Each proportion of the compound (a), compound (b), compound (c)and compound (d) in the composition for optical materials is notdetermined unequivocally because it depends on the refractive index orviscosity of each compound and the properties of the resulting resin. Tomaintain a high refractive index, the total amount of the compound (a)and the compound (d) is preferably 5 to 95 parts by weight. To enhancethe impact resistance, the total amount of the compound (b) and thecompound (c) is preferably 5 to 95 parts by weight. If exceeding theabove ranges, a high impact resistance intended by the present inventionis not achieved. In addition, there occur several disadvantages such asinsufficient heat resistance, discoloration of the cured product andfailure in achieving one of the objects of the present invention, i.e.,a high refractive index and a high Abbe's number. Preferably, the totalamount of the compound (a) and the compound (d) is 5 to 95 parts byweight and the total amount of the compound (b) and the compound (c) is5 to 95 parts by weight. More preferably, the total amount of thecompound (a) and the compound (d) is 10 to 90 parts by weight and thetotal amount of the compound (b) and the compound (c) is 10 to 90 partsby weight. Most preferably, the total amount of the compound (a) and thecompound (d) is 20 to 90 parts by weight and the total amount of thecompound (b) and the compound (c) is 10 to 90 parts by weight.

[0013] To further enhance the impact resistance of the optical materialobtained by polymerization curing, the compound (a) preferably has inone molecule two or more structure represented by Formula 1, and morepreferably the compound (a) is represented by the following Formula 2:

[0014] wherein R¹, R², R³, R⁴, Y, m and n are as defined in Formula 1;the compound (b) preferably has in one molecule two or more isocyanategroups and/or isothiocyanate groups; and the compound (c) preferably hasin one molecule two or more mercapto groups.

[0015] To achieve a high refractive index, one of the objects of thepresent invention, R¹ of Formula 1 representing the compound (a) ispreferably a C₀₋₂ hydrocarbon group, and each of R², R³ and R⁴ ofFormula 1 is preferably hydrogen or methyl group. More preferably, R¹ isa C₀₋₁ hydrocarbon group, and each of R², R³ and R⁴ is hydrogen. Apreferred compound (b) is one having a sulfur atom, and more preferredis one having a sulfide linkage. A preferred compound (c) is one havinga sulfur atom in addition to a mercapto group, and more preferred is onehaving a sulfide linkage. The compound (d) is an inorganic compound. Theinorganic compound referred to herein has the meaning described in“Standard Dictionary of Chemical Terms”, compiled by The ChemicalSociety of Japan, 1991, Maruzen. Namely, as described in the abovedocument, the inorganic compound referred to herein means compoundshaving no carbon atom and relatively simple compounds even when havingcarbon atom. Therefore, carbon disulfide, potassium thiocyanate, etc.which are generally not classified into organic compounds are regardedherein as inorganic compounds. The compound (d) is preferably at leastone compound selected from the group consisting of sulfur, carbondisulfide, selenium, selenium sulfide and lead selenide.

[0016] The compound (a) includes any compounds having in one molecule atleast one structure of Formula 1. Examples of preferred compounds are:

[0017] (A) Compounds having in one molecule at least one structure ofFormula 1 wherein n is zero;

[0018] (B) Compounds having in one molecule at least one structure ofFormula 1 wherein Y is O;

[0019] (C) Compounds having in one molecule at least one structure ofFormula 1 wherein Y is S;

[0020] (D) Compounds having in one molecule at least one structure ofFormula 1 wherein Y is Se; and

[0021] (E) Compounds having in one molecule at least one structure ofFormula 1 wherein Y is Te.

[0022] The compounds (A), (B), (C), (D) and (E) are mainly constitutedby a chain backbone, a branched backbone, an alicyclic backbone, anaromatic backbone or a heterocyclic backbone having nitrogen, oxygen,sulfur, selenium or tellurium. The compounds may have in one moleculetwo or more of these backbone structures simultaneously. The compoundsmay also have a sulfide linkage, a selenide linkage, a telluridelinkage, an ether linkage, a sulfone linkage, a ketone linkage, an esterlinkage, an amide linkage or a urethane linkage. (A) Preferred examplesof the compounds having in one molecule at least one structure ofFormula 1 wherein n is zero include: Organic compounds having aliphaticchain backbone:

[0023] 1,1-bis(epithioethyl)methane, 1,1-bis(epithioethyl)methane,1-(epithioethyl)-1-(p-epithiopropyl)methane,1,1-bis(β-epithiopropyl)methane, 1-(βepithioethyl)-1-(P-epithiopropyl)ethane, 1,2-bis(O-epithiopropyl)ethane,1,2-bis(β-epithiopropyl)ethane,1-(epithioethyl)-3-(β-epithiopropyl)butane,1,3-bis(,-epithiopropyl)propane,1-(epithioethyl)-4-(β-epithiopropyl)pentane,1,4-bis(,-epithiopropyl)butane,1-(epithioethyl)-5-(β-epithiopropyl)hexane,1-(epithioethyl)-2-(y-epithiobutylthio)ethane,1-(epithioethyl)-2-[2-(y-epithiobutylthio)ethylthio]ethane,tetrakis(,-epithiopropyl)methane, 1,1,1-tris(β-epithiopropyl)propane, 1,3-bis(p-epithiopropyl)- 1-(β-epithiopropyl)-2-thiapropane and 1,5-bis(,-epithiopropyl)-2,4-bis(,-epithiopropyl)-3-thiapentane; Compoundshaving alicyclic backbone:

[0024] 1,3- or 1,4-bis(epithioethyl)cyclohexane, 1,3- or1,4-bis(β-epithiopropyl)cyclohexane, bis[4-(epithioethyl)cyclohexyl]methane,bis[4-(β-epithiopropyl)cyclohexyl]methane,2,2-bis[4-(β-epithioethyl)cyclohexyl]propane,2,2-bis[4-(β-epithiopropyl)cyclohexyl]propane,bis[4-(β-epithiopropyl)cyclohexyl] sulfide,bis[4-(epithioethyl)cyclohexyl] sulfide,2,5-bis(epithioethyl)1,4-dithiane, 2,5-bis(β-epithiopropyl)-1,4-dithiane, 4-epithioethyl-1,2-cyclohexenesulfide, 4-epoxy-1,2-cyclohexene sulfide, 2,3-, 2,5-or2,6-bis(1,2-epithioethyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(2,3-epithiopropyl)-1,4-diselenane, 2,4-, 2,5- or2,6-bis(1,2-epithioethyl)-1,3-diselenane, 2,4-, 2,5- or2,6-bis(2,4-epithiopropyl)-1,3-diselenane, 2,3-, 2,5-, 2,6-or3,5-bis(1,2-epithioethyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(2,3-epithiopropyl)- 1-thia-4-selenane, 2,4- or 4,5-bis(1,2-epithioethyl)- 1,3-diselenolane, 2,4- or4,5-bis(2,4-epithiopropyl)-1,3-diselenolane, 2,4-, 2,5- or 4,5-bis(1,2-epithioethyl)- 1-thia-3-selenolane, 2,4-, 2,5- or 4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane, 2,3-, 2,4-, 2,5- or3,4-bis(1,2-epithioethyl)selenophane, 2,3-,2,4-, 2,5- or3,4-bis(2,3-epithiopropyl)selenophane, 2,3-, 2,5- or2,6-bis(1,2-epithioethyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(2,3-epithiopropyl)-1,4-ditellurane, 2,4-, 2,5- or2,6-bis(1,2-epithioethyl)-1,3-ditellurane, 2,4-, 2,5- or2,6-bis(2,4-epithiopropyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(1,2-epithioethyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or3,5-bis(2,3-epithiopropyl)-1-thia-4-tellurane, 2,4- or4,5-bis(1,2-epithioethyl)-1,3-ditellurolane, 2,4- or4,5-bis(2,4-epithiopropyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(1,2-epithioethyl)-1-thia-3-tellurolane 2,4-, 2,5- or4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane, 2,3-, 2,4-, 2,5- or3,4-bis(1,2-epithioethyl)tellurophane, and 2,3-, 2,4-, 2,5- or3,4-bis(2,3-epithiopropyl)tellurophane; Compounds having aromaticbackbone:

[0025] 1,3- or 1,4-bis(epithioethyl)benzene, 1,3- or1,4-bis(β-epithiopropyl)benzene, bis [4-(epithioethyl)phenyl]methane,bis[4-(β-epithiopropyl)phenyl]methane,2,2-bis[4-(epithioethyl)phenyl]propane,2,2-bis[4-(,-epithiopropyl)phenyl]propane, bis[4-(epithioethyl)phenyl]sulfide, bis[4-(β-epithiopropyl)phenyl] sulfide,bis[4-(epithioethyl)phenyl] sulfone, bis[4-(β-epithiopropyl)phenyl]sulfone, 4,4′-bis(epithioethyl)biphenyl, and 4,4═-bis(β-epithiopropyl)biphenyl; and Compounds obtained by replacing at leastone hydrogen of the epithio group in the above compounds with methyl.(B) Preferred examples of the compounds having in one molecule at leastone structure of Formula 1 wherein Y is O include: Organic compoundshaving aliphatic chain backbone:

[0026] bis(β-epithiopropyl) ether, bis(β-epithiopropyl) ether,bis(p-epithiopropyloxy)methane, 1,2-bis(β-epithiopropyloxy)ethane,1,3-bis(β-epithiopropyloxy)propane, 1,2-bis(β-epithiopropyloxy)propane,1-(β-epithiopropyloxy)-2-(β-epithiopropyloxymethyl)propane,1,4-bis(β-epithiopropyloxy)butane, 1,3-bis(β-epithiopropyloxy)butane,1-(β-epithiopropyloxy)-3-(β-epithiopropyloxymethyl)butane,1,5-bis(β-epithiopropyloxy)pentane,1-(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)pentane,1,6-bis(β-epithiopropyloxy)hexane, bis(epithioethyl) ether,1-(β-epithiopropyloxy)-5-(β-epithiopropyloxymethyl)hexane,1-(β-epithiopropyloxy)-2-[(2-β-epithiopropyloxyethyl)oxy]ethane,1-(β-epithiopropyloxy)-2-[[2-(2-0-epithiopropyloxyethyl)oxyethyl]oxy]ethane,bis(5,6-epithio-3-oxahexyl) selenide, bis(5,6-epithio-3-oxahexyl)telluride, tetrakis(β-epithiopropyloxymethyl)methane,1,1,1-tris(β-epithiopropyloxymethyl)propane,1,5-bis(β-epithiopropyloxy)-2-(β-epithiopropyloxymethyl)-3-thiapentane,1,5-bis(β-epithiopropyloxy)-2,4-bis(β-epithiopropyloxymethyl)-3-thiapentane,1-(β-epithiopropyloxy)-2,2-bis(β-epithiopropyloxymethyl)-4-thiahexane,1,5,6-tris(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)-3-thiahexane,1,8-bis(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-4,5-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-4,4-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-2,4,5-tris(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-2,5-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropyloxy)-5-(β-epithiopropyloxymethyl)-5-[(2-β-epithiopropyloxyethyl)oxymethyl]-3,7-dithianonane,1,10-bis(β-epithiopropyloxy)-5,6-bis[(2-0-epithiopropyloxyethyl)oxy]-3,6,9-trithiadecane,1,11-bis(β-epithiopropyloxy)-4,8-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyloxy)-5,7-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyloxy)-5,7-[(2-β-epithiopropyloxyethyl)oxymethyl]-3,6,9-trithiaundecane, and1,11-bis(β-epithiopropyloxy)-4,7-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane; Compounds havingalicyclic backbone:

[0027] 1,3- or 1,4-bis(β-epithiopropyloxy)cyclohexane, 1,3- or1,4-bis(β-epithiopropyloxymethyl)cyclohexane, bis[4-(β-epithiopropyloxy)cyclohexyl]methane,2,2-bis[4-(β-epithiopropyloxy)cyclohexyl]propane,bis[4-(β-epithiopropyloxy)cyclohexyl] sulfide,2,5-bis(β-epithiopropyloxymethyl)- 1,4-dithiane, 2,5-bis(β-epithiopropyloxyethyloxymethyl)- 1,4-dithiane, 2,4- or 4,5-bis(3,4-epithio-1-oxabutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-oxapentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-selenolane,bis(3,4-epithio-1-oxabutyl)tricycloselenaoctane, bis(3,4-epithio-1-oxabutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-oxabutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-oxapentyl)selenophane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-oxapenyyl)-1,4-diselenane, 2,4-,2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,3-diselenane, 2,4-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurolane, 2,4-or4,5-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-oxapentyl)- 1-thia-3-tellurolane, bis(3,4-epithio-1-oxabutyl)tricyclotelluraoctane,bis(3,4-epithio-1-oxabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-oxabutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epitho-2-oxapentyl)tellurophane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,4-ditellurane, 2,4-,2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurane, 2,4-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane, and 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-oxapentyl)-l-thia-4-tellurane; Compounds havingaromatic backbone:

[0028] 1,3- or 1,4-bis(β-epithiopropyloxy)benzene, 1,3- or1,4-bis(β-epithiopropyloxymethyl)benzene,bis[4-(β-epithiopropyl)phenyl]methane, 2,2-bis[4-(β-epithiopropylthio)phenyl]propane,bis[4-(β-epithiopropylthio)phenyl] sulfide,bis[4-(β-epithiopropylthio)phenyl] sulfone, and4,4′-bis(β-epithiopropylthio)biphenyl; and Compounds obtained byreplacing at least one hydrogen of the epithio group in the abovecompounds with methyl. (C) Preferred examples of the compounds having inone molecule at least one structure of Formula 1 wherein Y is S include:Organic compounds having aliphatic chain backbone:

[0029] bis(β-epithiopropyl) sulfide, bis(β-epithiopropyl) sulfide,bis(β-epithiopropyl) disulfide, bis(β-epithiopropyl) disulfide,bis(β-epithiopropyl) trisulfide, bis(β-epithiopropylthio)methane,1,2-bis(β-epithiopropylthio)ethane, 1,3-bis(β-epithiopropylthio)propane, 1,2-bis(β-epithiopropylthio)propane,bis(epithioethyl) sulfide, bis(epithioethyl) disulfide,1-(β-epithiopropylthio)-2-(β-epithiopropylthiomethyl)propane,1,4-bis(β-epithiopropylthio)butane, 1,3-bis(β-epithiopropylthio)butane,1-(β-epithiopropylthio)-3-(β-epithiopropylthiomethyl)butane,1,5-bis(β-epithiopropylthio)pentane,1-(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)pentane,1,6-bis(β-epithiopropylthio)hexane,1-(β-epithiopropylthio)-5-(β-epithiopropylthiomethyl)hexane,1-(β-epithiopropylthio)-2- [(2- β-epithiopropylthioethyl)thio]ethane,1-(D-epithiopropylthio)-2-[[2-(2-β-epithiopropylthioethyl)thioethyl]thio]ethane,tetrakis(β-epithiopropylthiomethyl)methane, 1,1,1-tris(β-epithiopropylthiomethyl)propane,1,5-bis(β-epithiopropylthio)-2-(β-epithiopropylthiomethyl)-3-thiapentane,1,5-bis(β-epithiopropylthio)-2,4-bis(β-epithiopropylthiomethyl)-3-thiapentane,1-(β-epithiopropylthio)-2,2-bis(β-epithiopropylthiomethyl)-4-thiahexane,1,5,6-tris(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)-3-thiahexane,1,8-bis(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-4,5-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-4,4-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-2,4,5-tris(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-2,5-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropylthio)-5-(β-epithiopropylthiomethyl)-5-[(2-0-epithiopropylthioethyl) thiomethyl]-3,7-dithianonane,1,10-bis(β-epithiopropylthio)-5,6-bis[(2-β-epithiopropylthioethyl)thio]-3,6, 9-trithiadecane,1,11-bis(β-epithiopropylthio)-4,8-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylthio)-5,7-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylthio)-5,7-[(2-β-epithiopropylthioethyl)thiomethyl]-3,6, 9-trithiaundecane,1,11-bis(β-epithiopropylthio)-4,7-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,tetra[2-(β-epithiopropylthio)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylthio)acetylmethyl]propane, tetra[2-(β-epithiopropylthiomethyl)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylthiomethyl)acetylmethyl]propane,bis(5,6-epithio-3-thiahexyl) selenide, 2,3-bis(6, 7-thioepoxy-1-selena-4-thiaheptyl)- 1-(3, 4-thioepoxy- 1-thiabutyl)propane, 1,1,3,3-tetrakis(4, 5-thioepoxy-2-thiapentyl)-2-selenapropane, bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy- 1-thiabutyl), 1 ,4-bis(3,4-thioepoxy-1-thiabutyl)-2, 3-bis(6, 7-thioepoxy- 1-selena-4-thiaheptyl)butane,tris(4, 5-thioepoxy-2-thiapentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-thiabutyl), bis(5,6-epithio-3-thiahexyl)telluride, 2,3-bis(6, 7-thioepoxy- 1-tellura-4-thiaheptyl)-1-(3,4-thioepoxy-1-thiabutyl)propane, 1,1,3, 3-tetrakis(4,5-thioepoxy-2-thiapentyl)-2-tellurapropane, bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thioepoxy-1-thiabutyl), 1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy- 1-tellura-4-thiaheptyl)butane andtris(4, 5-thioepoxy-2-thiapentyl)-3-tellura-6-thiaoctane- 1,8-bis(3,4-thioepoxy- 1-thiabutyl); Compounds having alicyclic backbone:

[0030] 1,3- or 1,4-bis(β-epithiopropylthio)cyclohexane, 1,3- or1,4-bis(β-epithiopropylthiomethyl)cyclohexane,bis[4-(β-epithiopropylthio)cyclohexyl]methane, 2,2-bis[4-(β-epithiopropylthio)cyclohexyl]propane,bis[4-(β-epithiopropylthio)cyclohexyl] sulfide, 2,5-bis(β-epithiopropylthiomethyl)- 1, 4-dithiane, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-thiabutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-thiapentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-thiabutyl)-1,3-diselenane, 2,4-, 2,5-or5,6-bis(4,5-epithio-2-thiapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(4,5-epithio-2-thiapentyl)- 1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio- 1-thiabutyl)- 1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-thiapentyl)-1,3-diselenolane, 2,4-, 2,5-or4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-selenolane,2,6-bis(4,5-epithio-2-thiapentyl)-1,3,5-triselenane,bis(3,4-epithio-1-thiabutyl)tricycloselenaoctane,bis(3,4-epithio-1-thiabutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-thiabutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-thiapentyl)selenophane, 2-(4,5-thioepoxy-2-thiapentyl)-5-(3 ,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane, 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-thiabutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane, 2,3-,2,5-, 2,6- or3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane, 2,3-, 2,5-,2,6-3,5-bis(4, 5-epithio-2-thiapentyl)-1-thia-4-tellurane, 2,4- or 4,5-bis(3,4-epithio- 1-thiabutyl)-1, 3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-thiapentyl)- 1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-tellurolane,2,6-bis(4,5-epithio 2-thiapentyl)-1,3, 5-tritellurane, bis(3, 4-epithio-1-thiabutyl)tricyclotelluraoctane,bis(3,4-epithio-1-thiabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1- thiabutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-thiapentyl)tellurophane, 2-(4,5-thioepoxy-2-thiapentyl)-5-(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane, and 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5-or 4,5-bis(4, 5-thioepoxy-2-thiapentyl)-1-telluracyclohexane; Compounds having aromatic backbone:

[0031] 1,3- or 1,4-bis(β-epithiopropylthio)benzene, 1,3- or1,4-bis(β-epithiopropylthiomethyl)benzene,bis[4-(β-epithiopropylthio)phenyl]methane,2,2-bis[4-(β-epithiopropylthio)phenyl]propane,bis[4-(β-epithiopropylthio)phenyl] sulfide,bis[4-(β-epithiopropylthio)phenyl] sulfone, and4,4′-bis(β-epithiopropylthio)biphenyl; and Compounds obtained byreplacing at least one hydrogen of the β-epithiopropyl group in theabove compounds with methyl. (D) Preferred examples of the compoundshaving in one molecule at least one structure of Formula 1 wherein Y isSe include: Organic compounds having aliphatic chain backbone:

[0032] bis(β-epithiopropyl) selenide, bis(β-epithiopropyl) selenide,bis(β-epithiopropyl) diselenide, bis(13-epithiopropyl) diselenide,bis(β-epithiopropyl) triselenide, bis(β-epithiopropylseleno)methane,1,2-bis(β-epithiopropylseleno)ethane,1,3-bis(β-epithiopropylseleno)propane,1,2-bis(β-epithiopropylseleno)propane, bis(epithioethyl) selenide,bis(epithioethyl) diselenide,1-(β-epithiopropylseleno)-2-(D-epithiopropylselenomethyl)propane,1,4-bis(β-epithiopropylseleno)butane,1,3-bis(β-epithiopropylseleno)butane,1-(β-epithiopropylseleno)-3-(β-epithiopropylselenomethyl)butane,1,5-bis(β-epithiopropylseleno) pentane,1-(β-epithiopropylseleno)-4-(β-epithiopropylselenomethyl)pentane,1,6-bis(β-epithiopropylseleno)hexane,1-(β-epithiopropylseleno)-5-(β-epithiopropylselenomethyl)hexane,1-(β-epithiopropylseleno)-2-[(2-β-epithiopropylselenoethyl)thio]ethane,1-(β-epithiopropylseleno)-2-[[2-(2-β-epithiopropylselenoethyl)selenoethyl]thio]ethane,tetrakis(β-epithiopropylselenomethyl)methane,1,1,1-tris(β-epithiopropylselenomethyl)propane, 1,5-bis(β-epithiopropylseleno)-2-(β-epithiopropylselenomethyl)-3-thiapentane,1, 5-bis(β-epithiopropylseleno)-2,4-bis(β-epithiopropylselenomethyl)-3-thiapentane,1-(β-epithiopropylseleno)-2,2-bis(β-epithiopropylselenomethyl)-4-thiahexane,1,5,6-tris(β-epithiopropylseleno)-4-(,-epithiopropylselenomethyl)-3-thiahexane, 1,8-bis(β-epithiopropylseleno)-4-(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-4,5-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-4,4-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-2,4,5-tris(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-2,5-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,9-bis(9-epithiopropylseleno)-5-(9-epithiopropylselenomethyl)-5-[(2-0-epithiopropylselenoethyl)]epithiopropylselenoethyl)selenomethyl]-3,7-dithianonane,1,10-bis(β-epithiopropylseleno)-5,6-bis[(2-β-epithiopropylselenoethyl)thio]-3,6,9-trithiadecane1,11-bis(β-epithiopropylseleno)-4,8-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-5,7-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-5, 7-[(2-β-epithiopropylselenoethyl)selenomethyl] -3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-4,7-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,tetra [2-(β-epithiopropylseleno)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylseleno)acetylmethyl]propane,tetra[2-(,β-epithiopropylselenomethyl)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylselenomethyl)acetylmethyl]propane,bis(5,6-epithio-3-selenohexyl) selenide, 2,3-bis(6, 7-thioepoxy-1-selena-4-selenoheptyl)- 1-(3,4-thioepoxy- 1-selenobutyl)propane,1,1,3, 3-tetrakis(4, 5-thioepoxy-2-selenopentyl)-2-selenapropane,bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy- 1-selenobutyl),1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6, 7-thioepoxy-1-selena-4-selenoheptyl)butane, tris(4,5-thioepoxy-2-selenopentyl)-3-selena-6-thiaoctane- 1,8-bis(3,4-thioepoxy- 1-selenobutyl), bis(5,6-epithio-3-selenohexyl)telluride, 2,3-bis(6,7-thioepoxy-1-tellura-4-selenoheptyl)-1-(3,4-thioepoxy- 1-selenobutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-selenopentyl)-2-tellurapropane, bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-tritelluraundecane-1,11-bis(3,4-thioepoxy- 1-selenobutyl),1,4-bis(3,4-thioepoxy- 1-selenobutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-selenoheptyl)butane and tris(4,5-thiepoxy-2-selenopentyl)-3-tellura-6-thiaoctane- 1,8-bis(3,4-thioepoxy- l-selenobutyl); Compounds having alicyclic backbone:

[0033] 1,3- or 1,4-bis(β-epithiopropylseleno)cyclohexane, 1,3- or1,4-bis(β-epithiopropylselenomethyl)cyclohexane,bis[4-(β-epithiopropylseleno)cyclohexyl] methane, 2,2-bis[4-(β-epithiopropylseleno)cyclohexyl]propane,bis[4-(β-epithiopropylseleno)cyclohexyl] sulfide,2,5-bis(β-epithiopropylselenomethyl)-1,4-dithiane, 2,5-bis(β-epithiopropylselenoethylthiomethyl)-1 ,4-dithiane, 2,3-2,5- or2,6-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio-1-selenobutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-selenopentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-selenobutyl)-l-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-selenolane,2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-triselenane,bis(3,4-epitbio-1-selenobutyl)tricycloselenaoctane,bis(3,4-epithio-1-selenobutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-selenobutyl)selenophane, 2,3-, 2,4-, 2,5-,3,4-bis(4,5-epithio-2-selenopentyl)selenophane,2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-selenacyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-selenacyclohexane, 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-selenacyclohexane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-selenobutyl)-I,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-selenopentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-selenobutyl)-1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-tellurane, 2,3-, 2,52,6- or3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-tellurane, 2,4- or4,5-bis(3,4-epithio1-selenobutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-telluroane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-tellurolane,2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-tritellurane,bis(3,4-epithio-1-selenobutyl)tricyclotelluraoctane, bis(3,4-epithio-1-selenobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1- selenobutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2- selenopentyl)tellurophane, 2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy- 1-selenobutyl)-1-telluracyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4- thioepoxy-1-selenobutyl)-1-telluracyclohexane, and 2,3-,2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4, 5-bis(4, 5-thioepoxy-2-selenopentyl)-1-telluracyclohexane; Compounds having aromatic backbone:

[0034] 1,3- or 1,4-bis(β-epithiopropylseleno)benzene, 1,3- or 1,4-bis(β-epithiopropylselenomethyl)benzene, bis[4-(D-epithiopropylseleno)phenyl]methane, 2,2-bis [4-(β-epithiopropylseleno)phenyl]propane, bis[4-(β-epithiopropylseleno)phenyl]sulfide, bis[4-(β-epithiopropylseleno)phenyl] sulfone and 4,4′-bis(β-epithiopropylseleno)biphenyl; and Compounds obtained by replacing atleast one hydrogen of the β-epithiopropyl group in the above compoundswith methyl. (E) Preferred examples of the compounds having in onemolecule at least one structure of Formula 1 wherein Y is Te include:Organic compounds having aliphatic chain backbone:

[0035] bis(β-epithiopropyl) telluride, bis(β-epithiopropyl) telluride,bis(β- epithiopropyl) ditelluride, bis(β-epithiopropyl) ditelluride,bis(β- epithiopropyl) tritelluride, bis(β-epithiopropyltelluro)methane,1,2-bis(β- epithiopropyltelluro)ethane, 1,3-bis(β-epithiopropyltelluro)propane, 1,2-bis(β-epithiopropyltelluro)propane, bis(epithioethyl) telluride,bis(epithioethyl) ditelluride,1-(β-epithiopropyltelluro)-2-(β-epithiopropyltelluromethyl)propane,1,4-bis(β-epithiopropyltelluro)butane,1,3-bis(β-epithiopropyltelluro)butane, 1-(β-epithiopropyltelluro)-3-(β-epithiopropyltelluromethyl)butane,1,5-bis(β- epithiopropyltelluro)pentane,1-(β-epithiopropyltelluro)-4-(β- epithiopropyltelluromethyl)pentane,1,6-bis(β-epithiopropyltelluro)hexane, 1-(,β-epithiopropyltelluro)-5-(β-epithiopropyltelluromethyl)hexane, 1-(β-epithiopropyltelluro)-2-[(2- β-epithiopropyltelluroethyl)thio]ethane,1-(β- epithiopropyltelluro)-2- [[2-(2-β-epithiopropyltelluroethyl)telluroethyl]thio]ethane, tetrakis(β-epithiopropyltelluromethyl)methane, 1,1,1-tris(β-epithiopropyltelluromethyl)propane,1,5-bis(β-epithiopropyltelluro)-2-(β-epithiopropyltelluromethyl)-3-thiapentane, 1, 5-bis(P-epithiopropyltelluro)-2, 4-bis(β-epithiopropyltelluromethyl)-3-thiapentane,1-(β-epithiopropyltelluro)-2,2-bis(β-epithiopropyltelluromethyl)-4-thiahexane, 1,5,6-tris(β-epithiopropyltelluro)-4-(β-epithiopropyltelluromethyl)-3-thiahexane,1,8-bis(β-epithiopropyltelluro)-4-(D-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,8- bis(β-epithiopropyltelluro)-4,5-bis(β-epithiopropyltelluromethyl)-3,6- dithiaoctane,1,8-bis(β-epithiopropyltelluro)-4,4-bis(β-epithiopropyltelluromethyl)-3, 6-dithiaoctane,1,8-bis(β-epithiopropyltelluro)- 2,4,5-tris(β-epithiopropyltelluromethyl)-3,6-dithiaoctane, 1,8-bis(β-epithiopropyltelluro)-2,5-bis(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropyltelluro)-5-(β-epithiopropyltelluromethyl)-5-[(2-β-epithiopropyltelluroethyl)selenomethyl] -3, 7-dithianonane, 1,10-bis(β-epithiopropyltelluro)-5,6-bis[(2-β-epithiopropyltelluroethyl)thio]-3,6,9-trithiadecane, 1,11-bis(β-epithiopropyltelluro)-4,8-bis(β-epithiopropyltelluromethyl)-3, 6,9-trithiaundecane, 1,11-bis(β-epithiopropyltelluro)-5, 7-bis(β-epithiopropyltelluromethyl)-3,6,9-trithiaundecane, 1,11-bis(β-epithiopropyltelluro)-5, 7-[(2-β-epithiopropyltelluroethyl)selenomethyl]-3,6,9-trithiaundecane,1,11-bis(β- epithiopropyltelluro)-4,7-bis(β-epithiopropyltelluromethyl)-3,6,9- trithiaundecane,tetra[2-(β-epithiopropyltelluro)acetylmethyl] methane, 1,1,1-tri[2-(D-epithiopropyltelluro)acetylmethyl]propane, tetra[2-(β-epithiopropyltelluromethyl)acetylmethyl]methane, 1,1,1-tri[2-(β-epithiopropyltelluromethyl)acetylmethyl]propane, bis(5,6-epithio-3-tellurohexyl) selenide, 2, 3-bis(6, 7-thioepoxy-1-selena-4-telluroheptyl)-1-(3,4- thioepoxy- 1-tellurobutyl)propane,1,1,3, 3-tetrakis(4, 5-thioepoxy-2- telluropentyl)-2-selenapropane,bis(4, 5-thioepoxy-2-telluropentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy-1-tellurobutyl),1,4-bis(3,4-thioepoxy- 1-tellurobutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-telluroheptyl)butane, tris(4, 5-thioepoxy-2-telluropentyl)-3-selena-6-thiaoctane- 1,8-bis(3,4-thioepoxy- 1- tellurobutyl), bis(5, 6-epithio-3-tellurohexyl)telluride, 2, 3-bis(6,7-thioepoxy- 1- tellura-4-telluroheptyl)-1-(3,4-thioepoxy- 1-tellurobutyl)propane, 1,1,3,3- tetrakis(4,5-thioepoxy-2-telluropentyl)-2-tellurapropane, bis(4, 5-thioepoxy-2-telluropentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thioepoxy-1-tellurobutyl), 1,4-bis(3, 4-thioepoxy-1-tellurobutyl)-2, 3-bis(6,7-thioepoxy- 1-tellura-4-telluroheptyl)butane and tris(4,5-thiepoxy-2-telluropentyl)-3-tellura-6- thiaoctane-1,8-bis(3,4-thioepoxy- 1-tellurobutyl); Compounds having alicyclicbackbone:

[0036] 1,3- or 1,4-bis(β-epithiopropyltelluro)cyclohexane, 1,3- or1,4-bis(β- epithiopropyltelluromethyl)cyclohexane, bis[4-(β-epithiopropyltelluro)cyclohexyl]methane, 2, 2-bis[4-(β-epithiopropyltelluro)cyclohexyl]propane, bis [4-(β-epithiopropyltelluro)cyclohexyl] sulfide,2,5-bis(β-epithiopropyltelluromethyl)- 1, 4-dithiane, 2,5-bis(β-epithiopropyltelluroethylthiomethyl)- 1, 4-dithiane, 2,3-, 2,5-or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-diselenane, 2,3-, 2,5- or2,6- bis(4,5-epithio-2-telluropentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio- 1-tellurobutyl)-1,3-diselenane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-telluropentyl)- 1,3-diselenane, 2,3-, 2,5-, 2,6-or 3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4- selenane, 2,3-, 2,5-,2,6- or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4- selenolane, 2,4-or 4,5-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-telluropentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4- epithio-1-tellurobutyl)-1-thia-3-selenoolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2- telluropentyl)- 1-thia-3-selenolane,2,6-bis(4,5-epithio-2-telluropentyl)- 1,3,5- triselenane, bis(3,4-epithio- 1-tellurobutyl)tricycloselenaoctane, bis(3, 4-epithio-1-tellurobutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1- tellurobutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2- telluropentyl)selenophane, 2-(4,5-thioepoxy-2-telluropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4- thioepoxy-1-tellurobutyl)-1-selenacyclohexane, 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-selenacyclohexane, 2,3-, 2,5-or 2,6- bis(3,4-epithio-1-tellurobutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2- telluropentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-tellurobutyl)- 1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-telluropentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6-or 3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-tellurane, 2,3-, 2,52,6- or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-tellurane, 2,4- or4,5-bis(3,4- epithio-1-tellurobutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2- telluropentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-tellurobutyl)- 1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-telluropentyl)-1-thia-3- tellurolane, 2,6-bis(4,5-epithio-2-telluropentyl)-1,3,5-tritellurane, bis(3,4-epithio-l-tellurobutyl)tricyclotelluraoctane, bis(3,4-epithio- 1-tellurobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1- tellurobutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2- telluropentyl)tellurophane, 2-(4,5-thioepoxy-2-telluropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-or 4,5- bis(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane, and2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-telluracyclohexane; Compoundshaving aromatic backbone:

[0037] 1,3- or 1,4-bis(β-epithiopropyltelluro)benzene, 1,3- or1,4-bis(β- epithiopropyltelluromethyl)benzene, bis[4-(β-epithiopropyltelluro)phenyl] methane, 2,2-bis [4-(β-epithiopropyltelluro)phenyl]propane, bis[4-(β-epithiopropyltelluro)phenyl] sulfide,bis[4-(D-epithiopropyltelluro)phenyl] sulfone, and 4,4′-bis(β-epithiopropyltelluro)biphenyl; and Compounds obtained by replacing atleast one hydrogen of the β-epithiopropyl group in the above compoundswith methyl.

[0038] The compounds (A) to (E) may include those having an unsaturatedgroup. Examples thereof include vinylphenyl thioglycidyl ether,vinylbenzyl thioglycidyl ether, thioglycidyl methacrylate, thioglycidylacrylate and allyl thioglycidyl ether.

[0039] The compound (a) is not limited to those mentioned above and maybe used alone or in combination of two or more.

[0040] Of the above compounds, preferred are the compounds (B) having inone molecule at least one structure of Formula 1 wherein Y is 0, thecompounds (C) having in one molecule at least one structure of Formula 1wherein Y is S, the compounds (D) having in one molecule at least onestructure of Formula 1 wherein Y is Se. More preferred are the compounds(C) and (D). Still more preferred are the compounds (C) and (D) whereinm is 1 or 2, and n is 1 or 2, and the most preferred are the compounds(C) and (D) wherein m is 1 and n is 1 or 2.

[0041] Examples of the most preferred compounds includebis(β-epithiopropyl) sulfide, bis(β-epithiopropyl) disulfide,bis(β-epithiopropyl) selenide, bis(, - epithiopropyl) diselenide, andcompounds having two or more β- epithiopropylthio groups orβ-epithiopropylseleno groups together with the chain backbone, thebranched backbone, the alicyclic backbone, the aromatic backbone or theheterocyclic backbone mentioned above. Especially preferred of the aboveare chain or branched compounds having two or more β- epithiopropylthiogroups or β-epithiopropylseleno groups, bis(β-epithiopropyl) sulfide,bis(β-epithiopropyl) disulfide, bis(β-epithiopropyl) selenide, andbis(,β- epithiopropyl) diselenide.

[0042] The compound (b) includes any compounds having in one molecule atleast one isocyanate group and/or isothiocyanate group. Examples thereofinclude isocyanate compounds such as methyl isocyanate, ethylisocyanate, propyl isocyanate, isopropyl isocyanate, n-butyl isocyanate,sec-butyl isocyanate, tert-butyl isocyanate, pentyl isocyanate, hexylisocyanate, octyl isocyanate, dodecyl isocyanate, cyclohexyl isocyanate,phenyl isocyanate, tolyl isocyanate, diethylene diisocyanate,tetramethylene diisocyanate, hexamethylene diisocyanate,trimethylhexamethylene diisocyanate, cyclohexane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,2,6-bis(isocyanatomethyl)decahydronaphthalene, lysine triisocyanate,2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, o- tolydynediisocyanate, 4,4′-diphneylmethane diisocyanate, diphenyl etherdiisocyanate, 3-(2′-isocyanatocyclohexyl)propyl isocyanate,tris(phenylisocyanate) thiophosphate, isopropylidenebis(cyclohexylisocyanate), 2,2′-bis(4-isoisocyanatophenyl)propane,triphenylmethane triisocyanate, bis(diisocyanatotolyl)phenylmethane,4,4′, 4″-triisocyanato-2,5- dimethoxyphenylamine, 3,3′-dimethoxybenzidine-4,4′-diisocyanate, 1,3- phenylene diisocyanate,1,4-phenylene diisocyanate, 4,4′-diisocyanatobiphenyl,4,4′-diisocyanato-3, 3′-dimethylbiphenyl,dicyclohexylmethan-4,4′-diisocyanate,1,1′-methylenebis(4-isocyanatobenzene), 1,1′-methylenebis(3-methyl-4-isocyanatobenzene), m-xylylene diisocyanate, β-xylylene diisocyanate,1,3- bis(1-isocyanato- 1 -methylethyl)benzene, 1,4-bis(1-isocyanato- 1-methylethyl)benzene, 1,3-bis(2-isocyanato-2-propyl)benzene, 2,6-bis(isocyanatomethyl)naphthalene, 1,5-naphthalene diisocyanate,bis(isocyanatomethyl)tetrahydrodicyclopentadiene,bis(isocyanatomethyl)dicyclopentadiene,bis(isocyanatomethyl)tetrahydrothiophene,2,5-diisocyanatomethylnorbornene, bis(isocyanatomethyl)adamantane,dimeric acid diisocyanate, 1,3,5-tri(1- isoisocyanatohexyl)isocyanuricacid, thiodiethyl diusocyanate, thiodipropyl diisocyanate, thiodihexyldiisocyanate, bis[(4-isocyanatomethyl)phenyl] sulfide, 2,5-diisocyanato- 1,4-dithiane, 2,5-diisocyanatomethyl- 1 ,4-dithiane,2,5- diisocyanatomethyl thiophene, dithiodiethyl diisocyanate, anddithiodipropyl diisocyanate; and compounds derived from the aboveisocyanate compounds by replacing all or a part of the isocyanate groupthereof with isothiocyanate group. The polyisocyanate compoundsmentioned above includes dimers produced by biuret reaction, cyclictrimers, alcohol adducts and thiol adducts.

[0043] The compound (b) is not limited to those mentioned above and maybe used alone or in combination of two or more. Preferred compounds (b)are those having in one molecule two or more isocyanate groups and/orisothiocyanate groups.

[0044] The compound (c) includes any compounds having in one molecule atleast one mercapto group. Examples thereof include mercaptans such asmethyl mercaptan, ethyl mercaptan, n-propyl mercaptan, n-butylmercaptan, allyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan,n-decyl mercaptan, n- dodecyl mercaptan, n-tetradecyl mercaptan,n-hexadecyl mercaptan, n- octadecyl mercaptan, cyclohexyl mercaptan,isopropyl mercaptan, tert-butyl mercaptan, tert-nonyl mercaptan,tert-dodecyl mercaptan, phenyl mercaptan, benzyl mercaptan,3-methylphenyl mercaptan, 4-methylphenyl mercaptan, 4- chlorobenzylmercaptan, 4-vinylbenzyl mercaptan, 3-binylbenzyl mercaptan, methylmercaptopropionate, ethyl thioglycolate, n-butyl thioglycolate, n-octylthioglycolate, methyl 3-mercaptopropionate, ethyl 3-mercaptopropionate,3- methoxybutyl 3-mercaptopropionate, n-butyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, n-octyl 3-mercaptopropionate, 2-mercaptoethanol, 3-mercapto- 1, 2-propanediol, 2-mercapto-1,3-propanediol, mercaptoacetic acid, mercaptoglycolic acid,mercaptopropionic acid, methanedithiol, methanetrithiol,3-mercaptopropanol, 2-mercaptopropanol, 2- phenyl-2-mercaptoethanol,1,2-dimercaptoethane, 1,2-dimercaptopropane, 1,3- dimercaptopropane, 2,2-dimercaptopropane, 1,4-dimercaptobutane, 1,6- dimercaptohexane,bis(2-mercaptoethyl) ether, bis(2-mercaptoethyl) sulfide, 1,2-bis(2-mercaptoethyloxy)ethane, 1, 2-bis(2-mercaptoethylthio)ethane,2,3- dimecrapto- 1-propanol, 1, 3-dimercapto-2-propanol, 1,2,3-trimercaptopropane, 2-mercaptomethyl- 1, 3-dimercaptopropane,2-mercaptomethyl- 1,4- dimercaptobutane,2-(2-mercaptoethylthio)-1,3-dimercaptopropane, 4- mercaptomethyl- 1,8-dimercapto-3, 6-dithiaoctane, 2,4-dimercaptomethyl- 1,5- dimercapto-3-thiapentane, 4, 8-dimercaptomethyl- 1,11 -dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl- 1,11-dimercapto-3,6,9-trithiaundecane, 5, 7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,1-tris(mercaptomethyl)propane, tetrakis(mercaptomethyl)methane, ethyleneglycol bis(2-mercaptoacetate), ethylene glycolbis(3-mercaptopropionate), diethylene glycol bis(2-mercaptoacetate),diethylene glycol bis(3- mercaptopropionate), 1,4-butanediolbis(2-mercaptoacetate), 1,4-butanediol bis(3-mercaptopropionate),trimethylolpropane tris(2-mercaptoacetate), trimethylolpropanetris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 1,2-dimercaptocyclohexane, 1,3-dimercaptocyclohexane, 1,4-dimercaptocyclohexane, 1, 3-bis(mercaptomethyl)cyclohexane, 1,4-bis(mercaptomethyl)cyclohexane, 2, 5-bis(mercaptomethyl)- 1, 4-dithiane,2,5- bis(2-mercaptoethyl)-1,4-dithiane, 2,5-bis(2-mercaptoethylthiomethyl)- 1,4- dithiane, 2,5-bis(mercaptomethyl)- 1-thiane, 2, 5-bis(2-mercaptoethyl)-1-thiane,2,5-bis(mercaptomethyl)thiophene, thiophenol, 4-tert-butylthiophenol, 2-methylthiophenol, 3-methylthiophenol, 4-methylthiophenol,2-vinylthiophenol, 3-vinylthiophenol, 4-vinylthiophenol,2-hydroxythiophenol, 3- hydroxythiophenol, 4-hydroxythiophenol,1,2-dimercaptobenzene, 1,3- dimercaptobenzene, 1,4-dimercaptobenzene,1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 2,2′-dimercaptobiphenyl, 4,4′- dimercaptobiphenyl,bis(4-mercaptophenyl)methane, 2,2-bis(4- mercaptophenyl)propane,bis(4-mercaptophenyl) ether, bis(4-mercaptophenyl) sulfide,bis(4-mercaptophenyl) sulfone, bis(4-mercaptomethylphenyl)methane, 2,2-bis(4-mercaptomethylphenyl)propane, bis(4-mercaptomethylphenyl) ether,bis(4-mercaptomethylphenyl) sulfide, mercaptobenzoic acid, 2-mercaptoimidazole, 2-mercapto- 1-methylimidazole, 2, 5-dimercapto-1,3,4- thiadiazole, 3,4-thiophenedithiol, glyceryl dithioglycolate,2-selenoethanol, bis(2-mercaptoethyl) selenide,bis(1,3-dimercapto-2-propyl) selenide, 2,3- bis(mercaptoethylseleno)-1-propanethiol, 2-mercaptomethyl- 1,5-dimercapto-3-. selenapentane,4,8-bis(mercaptomethyl)- 1,11-dimercapto-3, 9-dithia-6- selenaundecane,4, 8-bis(mercaptomethyl)- 1,11-dimercapto-6-thia-3,9- diselenaundecane,4,8-bis(mercaptomethyl)- 1,11-dimercapto-3, 6,9- triselenaundecane,bis(hydroxymercaptoethylselenomethyl)benzene, 1,4- dimercapto-2,3-bis(mercaptoethylseleno)butane, 1,2,3,4-tetrakis(mercaptoethylseleno)butane,1,9-dimercapto-5,5-bis(mercaptomethyl)- 3, 7-diselenanonane,tris(mercaptomethyl)- 1,8-dimercapto-6-thia-3- selenaoctane,bis(mercaptoethylselenomethyl)benzene, 2,5-diseleno- 1,4- dithiane, 2,5-bis(selenomethyl)- 1,4-dithiane, 2,5- bis(mercaptoethylselenomethyl)-1,4-dithiane, 2,6-dimercapto- 1-selena-4-thiane, 3,5-dimercapto-1-selena-4-thiane, 2,6-bis(mercaptomethyl)- 1-selena-4-thiane, 3,5-bis(mercaptomethyl)- 1-selena-4-thiane, 2,5-dimercapto-1,4-diselenane, 2,6- dimercapto- 1,4-diselenane,2,5-bis(mercaptomethyl)- 1, 4-diselenane, 2,6- bis(mercaptomethyl)- 1,4-diselenane, 2, 5-dimercaptoselenane, 3,4- dimercaptoselenane,2,5-bis(mercaptomethyl)selenane, 3,4- bis(mercaptomethyl)selenane, 2,5-bis(selenomethyl)selenane, 3,4- bis(selenomethyl)selenane, 4,5-dimercapto- 1, 3-diselenorane, 4,5- bis(dimercapto)-1,3-diselenorane,3,6-dimercaptotriselenocyclooctane, 3,6-bis(mercaptomethyl)triselenocyclooctane,3,6-diselenotriselenocyclooctane, and3,6-bis(selenomethyl)triselenocycloocatane. The polymercaptans mentionedabove include oligomers of about 2 to 20 polymerization degree.

[0045] The compound (c) is not limited to those mentioned above and maybe used alone or in combination of two or more. Preferred compounds (c)are those having in one molecule two or more mercapto groups. Morepreferred are those having a sulfur atom in addition to the mercaptogroups, and still more preferred are those having a sulfide linkage.

[0046] The compound (d) includes any inorganic compounds having at leastone sulfur atom and/or selenium atom. The total amount of sulfur atomand/or selenium atom in the inorganic compound is preferably 30% byweight or more. When the amount is less than 30%, the effect ofincreasing the refractive index of resin is lowered because the amountof sulfur atom and/or selenium atom in the composition for opticalmaterials increases not so much.

[0047] Examples of the inorganic compounds having sulfur atom includesulfur, hydrogen sulfide, carbon disulfide, carbon selenosulfide,ammonium sulfide, sulfur oxides such as sulfur dioxide and sulfurtrioxide, salts of thiocarbonic acid, sulfuric acid, salts of sulfuricacid, salts of hydrogensulfuric acid, salts of sulfurous acid, salts ofhyposulfurous acid, salts of persulfuric acid, salts of thiocyanic acid,salts of thiosulfuric acid, halides such as sulfur dichloride, thionylchloride and thiophosgen, boron sulfide, nitrogen sulfide, siliconsulfide, phosphorus sulfide, arsenic sulfide, selenium sulfide, metalsulfides and metal hydrogensulfides. Among these compounds, sulfur,carbon disulfide, phosphorus sulfide, selenium sulfide, metal sulfidesand metal hydrogensulfides are preferable, and sulfur, carbon disulfideand selenium sulfide are more preferable.

[0048] Examples of the inorganic compounds having selenium atom include,in addition to carbon selenosulfide and selenium sulfide mentioned aboveas the examples for the inorganic compound having sulfur atom, selenium,hydrogen selenide, selenium dioxide, carbon diselenide, ammoniumselenide, oxides of selenium such as selenium dioxide, selenic acid,salts of selenic acid, selenous acid, salts of selenous acid, salts ofhydrogenselenic acid, selenosulfuric acid, salts of selenosulfuric acid,selenopyrosulfuric acid, salts of selenopyrosulfuric acid, halides suchas selenium tetrabromide and selenium oxychloride, salts of selenocyanicacid, boron selenide, phosphorus selenide, arsenic selenide and metalselenides. Among these compounds, selenium, carbon diselenide,phosphorus selenide and metal selenides are preferable, and selenium andcarbon diselenide are more preferable. These inorganic compounds havingat least one sulfur atom and/or selenium atom may be used alone or incombination of two or more.

[0049] The compound (d) is not limited to those mentioned above and maybe used alone or in combination of two or more.

[0050] The composition of the present invention comprising the compound(a), compound (b), compound (c) and compound (d) is polymerized to aresin under heating in the presence or absence of a curing catalyst,preferably in the presence of a curing catalyst. As the curing catalyst,usable are amines, quaternary ammonium salts, phosphines, quaternaryphosphonium salts, tertiary sulfonium salts, secondary iodonium salts,mineral acids, Lewis acids, organic acids, silicic acids,tetrafluoroboric acids, peroxides, azo compounds, condensates ofaldehyde and amine compound, guanidine compounds, thiourea compounds,thiazole compounds, sulfenamide compounds, thiuram compounds, salts ofdithiocarbamic acid, salts of xanthogenic acid, and acid phosphates.

[0051] Examples of the curing catalysts are mentioned below. (1) AminesPrimary amines such as ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, isobutylamine, tert-butylamine, pentylamine,hexylamine, heptylamine, octylamine, decylamine, laurylamine,myristylamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine,allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol,aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine,3-propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine,3-isobutoxypropylamine, 3-(2- ethylhexyloxy)propylamine,aminocyclopentane, aminocyclohexane, aminonorbornene,aminomethylcyclohexane, aminobenzene, benzylamine, phenetylamine,a-phenylethylamine, naphthylamine and furfurylamine; primary polyaminessuch as ethylenediamine, 1,2-diaminopropane, 1,3- diaminopropane,1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane,1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine,bis-(3- aminopropyl) ether, 1,2-bis(3-aminopropoxy)ethane,1,3-bis(3-aminopropoxy)- 2,2′-dimethylpropane, aminoethylethanolamine,1,2-, 1,3- or 1,4- bisaminocyclohexane, 1,3- or1,4-bisaminomethylcyclohexane, 1,3- or 1,4- bisaminoethylcyclohexane,1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated4,4′-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine,N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine,N-aminopropylmorpholine, isophoronediamine, menthanediamine,1,4-bisaminopropylpiperadine, o-, m- or β-phenylenediamine, 2,4- or2,6-tolylenediamine, 2,4-toluenediamine, m- aminobenzylamine,4-chloro-o-phenylenediamine, tetrachloro-β- xylylenediamine,4-methoxy-6-methyl-m-phenylenediamine, m- or β- xylylenediamine, 1,5- or2,6-naphthalenediamine, benzidine, 4,4′-bis(o- toluidine), dianisidine,4,4′-diaminodiphenylmethane, 2,2-(4,4′- diaminodiphenyl)propane,4,4′-diaminodiphenyl ether, 4,4′-thiodianiline, 4,4′- diaminodiphenylsulfone, 4,4′-diaminoditolyl sulfone, methylenebis(o- chloroaniline),3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane,diethylenetriamine, iminobispropylamine, methyliminobispropylamine,bis(hexamethylene)triamine, triethylenetetramine,tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperadine,N-aminopropylpiperadine, 1,4-bis(aminoethylpiperadine),1,4-bis(aminopropylpiperadine), 2,6- diaminopyridine, andbis(3,4-diaminophenyl) sulfone; secondary amines such as diethylamine,dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine,di-n-pentylamine, di-3-pentylamine, dihexylamine, dioctylamine,di(2-ethylhexyl)amine, methylhexylamine, diallylamine, pyrrolidine,piperidine, 2-, 3- or 4-picoline, 2,4-, 2,6- or 3,5-lupetidine,diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine,methylbenzylamine, dinaphthylamine, pyrrol, indoline, indole, andmorpholine; secondary polyamines such as N,N′-dimethylethylenediamine,N,N′-dimethyl- 1, 2-diaminopropane, N,N′-dimethyl- 1, 3-diaminopropane,N,N′- dimethyl- 1,2-diaminobutane, N,N′-dimethyl- 1, 3-diaminobutane,N,N′- dimethyl- 1,4-diaminobutane, N,N′-dimethyl- 1, 5-diaminopentane,N,N′- dimethyl- 1 ,6-diaminohexane, N, N′-dimethyl-1, 7-diaminoheptane,N,N′- diethylethylenediamine, N, N′-diethyl- 1,2-diaminopropane, N,N′-diethyl- 1,3- diaminopropane, N, N′-diethyl- 1, 2-diaminobutane, N,N′-diethyl- 1,3- diaminobutane, N, N′-diethyl- 1, 4-diaminobutane, N,N′-diethyl- 1,6- diaminohexane, piperadine, 2-methylpiperadine, 2,5- or2,6- dimethylpiperadine, homopiperadine, 1,1-di(4-piperidyl)methane,1,2-di(4- piperidyl)ethane, 1,3-di(4-piperidyl)propane, and1,4-di(4-piperidyl)butane; tertiary amines such as trimethylamine,triethylamine, tri-n-propylamine, triisopropylamine,tri(1,2-dimethylpropyl)amine, tri(3-methoxypropyl)amine,tri-n-butylamine, triisobutylamine, tri-sec-butylamine,tri-n-pentylamine, tri- 3-pentylamine, tri-n-hexylamine,tri-n-octylamine, tri(2-ethylhexyl)amine, tridodecylamine,trilaurylamine, dicyclohexylethylamine, cyclohexyldiethylamine,tricyclohexylamine, N,N-dimethylhexylamine, N- methyldihexylamine,N,N-dimethylcyclohexylamine, N- methyldicyclohexylamine,N,N-diethylethanolamine, N,N- dimethylethanolamine,N-ethyldiethanolamine, triethanolamine, tribenzylamine,N,N-dimethylbenzylamine, diethylbenzylamine, triphenylamine,N,N-dimethylamino-β-cresol, N, N- dimethylaminomethylphenol,2-(N,N-dimethylaminomethyl)phenol, N,N- dimethylaniline,N,N-diethylaniline, pyridine, quinoline, N-methylmorpholine,N-methylpiperidine, and 2-(2-dimethylaminoethoxy)-4-methyl- 1,3,2-dioxabornane; tertiary polyamines such as tetramethylethylenediamine,pyrazine, N,N′-dimethylpiperadine, N,N′-bis(2-hydroxypropyl)piperadine,hexamethylenetetramine, N,N,N′,N′-tetramethyl- 1, 3-butaneamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N, N, N-tris(3-dimethylaminopropyl)amine, 2,4,6-tris(N, Nβ-dimethylaminomethyl)phenol,and heptamethylisobiguanide; imidazole compounds such as imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole,2- ethylimidazole, 4-ethylimidazole, N-butylimidazole, 2-butylimidazole,N- undecylimidazole, 2-undecylimidazole, N-phenylimidazole,2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole,2-mercaptoimidazole, 2-mercapto-N- methylimidazole,2-mercaptobenzimidazole, 3-mercapto-4-methyl-4H- 1,2,4- triazole,5-mercapto- 1-methyl-tetrazole, 2, 5-dimercapto- 1, 3,4-thiadiazole, 1-benzyl-2-methylimidazole, N-(2′-cyanoethyl)-2-methylimidazole, N-(2′-cycanoethyl)-2-undecylimidazole, N-(2′-cyanoethyl)-2-phenylimidazole,3,3-bis- (2-ethyl-4-methylimidazolyl)methane, and addition products ofalkylimidazoles and isocyanuric acid; and amidine compounds such as 1,8-diazabicyclo [5.4.0]undecene-7, 1, 5-diazabicyclo[4.3.0]nonene-5, and 6-dibutylamino- 1,8-diazabicyclo[5.4.0]undecene-7. (2) Complexes of amines(1) and borane or boron trifluoride. (3) Phosphines Trimethylphosphine,triethylphosphine, triisopropylphosphine, tri-n- butylphosphine,tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine,triphenylphosphine, tribenzylphosphine, tris(2- methylphenyl)phosphine,tris(3-methylphenyl)phosphine, tris(4- methylphenyl)phosphine,tris(diethylamino)phosphine, tris(4- methylphenyl)phosphine,dimethylphenylphosphine, diethylphenylphosphine,dicyclohexylphenylphosphine, ethyldiphenylphosphine,diphenylcyclohexylphosphine, and chlorodiphenylphosphine. (4) Quaternaryammonium salts Tetramethylammonium chloride, tetramethylammoniumbromide, tetramethylammonium acetate, tetraethylammonium chloride,tetraethylammonium bromide, tetraethylammonium acetate, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium iodide, tetra-n-butylammonium acetate, tetra-n-butylammonium borohydride, tetra-n-butylammonium hexafluorophosphite, tetra-n-butylammoniumhydrogensulfite, tetra-n-butylammonium tetrafluoroborate,tetra-n-butylammonium tetraphenylborate, tetra-n-butylammoniumβ-toluenesulfonate, tetra-n- hexylammonium chloride,tetra-n-hexylammonium bromide, tetra-n- hexylammonium acetate,tetra-n-octylammonium chloride, tetra-n- octylammonium bromide,tetra-n-octylammonium acetate, trimethyl-n- octylammonium chloride,trimethyldecylammonium chloride, trimethyldodecylammonium chloride,trimethylcetylammonium chloride, trimethyllaurylammonium chloride,trimethylbenzylammonium chloride, trimethylbenzylammonium bromide,triethyl-n-octylammonium chloride, triethylbenzylammonium chloride,triethylbenzylammonium bromide, tri-n- butyl-n-octylammonium chloride,tri-n-butylbenzylammonium fluoride, tri-n- butylbenzylammonium chloride,tri-n-butylbenzylammonium bromide, tri-n- butylbenzylammonium iodide,n-butyldimethylbenzylammonium chloride, n- octyldimethylbenzylammoniumchloride, decyldimethylbenzylammonium chloride,dodecyldimethylbenzylammonium chloride, cetyldimethylbenzylammoniumchloride, lauryldimethylbenzylammonium chloride, methyltriphenylammoniumchloride, methyltribenzylammonium chloride, methyltriphenylammoniumbromide, methyltribenzylammonium bromide, ethyltriphenylammoniumchloride, ethyltribenzylammonium chloride, ethyltriphenylammoniumbromide, ethyltribenzylammonium bromide, n- butyltriphenylammoniumchloride, n-butyltribenzylammonium chloride, n- butyltriphenylammoniumbromide, n-butyltribenzylammonium bromide, 1- methylpyridinium chloride,1-methylpyridinium bromide, 1-ethylpyridinium chloride,1-ethylpyridinium bromide, 1-n-butylpyridinium chloride, 1-n-butylpyridinium bromide, 1-n-hexylpyridinium chloride,1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide,1-n-dodecylpyridinium chloride, 1-n- dodecylpyridinium bromide,1-n-cetylpyridinium chloride, 1-n-cetylpyridinium bromide,1-phenylpyridinium chloride, 1-phenylpyridinium bromide, 1-benzylpyridinium chloride, 1-benzylpyridinium bromide,1-methylpicolinium chloride, 1-methylpicolinium bromide,1-ethylpicolinium chloride, 1- ethylpicolinium bromide,1-n-butylpicolinium chloride, 1-n-butylpicolinium bromide,1-n-hexylpicolinium chloride, 1-n-hexylpicolinium bromide, 1-n-octylpicolinium chloride, 1-n-octylpicolinium bromide,1-n-dodecylpicolinium chloride, 1-n-dodecylpicolinium bromide,1-n-cetylpicolinium chloride, 1-n- cetylpicolinium bromide,1-phenylpicolinium chloride, 1-phenylpicolinium bromide,1-benzylpicolinium chloride, and 1-benzylpicolinium bromide. (5)Phosphonium salts Tetramethylphosphonium chloride,tetramethylphosphonium bromide, tetraethylphosphonium chloride,tetraethylphosphonium bromide, tetra-n- butylphosphonium chloride,tetra-n-butylphosphonium bromide, tetra-n- butylphosphonium iodide,tetra-n-hexylphosphonium bromide, tetra-n- octylphosphonium bromide,methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide,ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide,n-butyltriphenylphosphonium bromide, n- butyltriphenylphosphoniumiodide, n-hexyltriphenylphosphonium bromide, n-octyltriphenylphosphonium bromide, tetraphenylphosphonium bromide,tetrakishydroxymethylphosphonium chloride,tetrakishydroxymethylphosphonium bromide,tetrakishydroxyethylphosphonium chloride, andtetrakishydroxybutylphosphonium chloride. (6) Sulfonium saltsTrimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide,tri-n-butylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate,tri-n-hexylsulfonium bromide, tri-n-octylsulfonium bromide,triphenylsulfonium chloride, triphenylsulfonium bromide, andtriphenylsulfonium iodide. (7) Iodonium salts Diphenyliodonium chloride,diphenyliodonium bromide, and diphenyliodonium iodide. (8) Mineral acidsHydrochloric acid, sulfuric acid, nitric acid, phosphoric acid andcarbonic acid, and half esters of the mineral acids. (9) Lewis AcidBoron trifluoride, boron trifluoride etherate, aluminum fluoride,aluminum chloride, triphenylaluminum, potassium octanoate, calciumacetate, tetraisopropoxytitanium, tetrabutoxytitanium,tetrachlorotitanium, 2- ethylhexyl titanate, dimethyltin oxide,dimethyltin dichloride, dibutyltin diacetate, dibutyltin acetate,dibutyltin dilaurate, dibutyltin laurate, dibutyltin octanoate,dibutyltin bis(dodecylmercaptide), dibutyltinbis(isooctylthioglycolate), dibutyltin oxide, butyltin trichloride,dibutyltin dichloride, tributyltin chloride, tetrabutyltin, dioctyltindiacetate, dioctyltin acetate, dioctyltin dilaurate, dioctyltin laurate,dioctyltin diricinolate, dioctyltin dioleate, dioctyltindi(6-hydroxy)caproate, dioctyltin bis(isooctylthoglycolate), dioctyltinoxide, dioctyltin dichloride, dioctyltin maleate, dioctyltinbis(butylmaleate), didodecyltin diricinolate, tin stearate, zincchloride, zinc acetylacetonate, copper oleate, copper acetylacetonate,iron acetylacetonato, iron naphthenate, iron lactate, iron citrate, andiron gluconate. (10) Organic acids and their half esters (11) Silicicacid and tetrafluoroboric acid (12) Peroxides Cumyl peroxyneodecanoate,diisopropyl peroxydicarbonate, diallyl peroxydicarbonate, di-n-propylperoxydicarbonate, dimyristyl peroxydicarbonate, cumylperoxyneohexanoate, tert-hexyl peroxyneodecanoate, tert-butylperoxyneodecanoate, tert-hexyl peroxyneohexanoate, tert-butylperoxyneohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide,dicumyl peroxide, di-tert-butyl peroxide, cumene hydroperoxide, andtert-butyl hydroperoxide. (13) Azo compounds 2,2′-Azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(2-cyclopropylpropionitrile), 2, 2′-azobis(2,4-dimethylvaleronitrile),2,2′- azobisisobutylonitrile, 2,2′-azobis(2-methylbutylonitrile), 1,1′-azobis(cyclohexane- 1-carbonitrile), 1-[(1-cyano-1-methyl)azo]formamide, 2- pneylazo-4-methoxy-2,4-dimethylvaleronitrile,2,2′-azobis(2-methylpropane), and 2, 2′-azobis(2, 4,4-trimethylpentane).(14) Condensates of aldehyde and amine compound Reaction product ofacetaldehyde and ammonia, condensate of formaldehyde and β-toluidine,condensate of acetaldehyde and β-toluidine, reaction product offormaldehyde and aniline, reaction product of acetaldehyde and aniline,reaction product of butylaldehyde and aniline, reaction product offormaldehyde, acetaldehyde and aniline, reaction product ofacetaldehyde, butylaldehyde and aniline, condensate of butylaldehyde andmonobutylamine, reaction product of butylaldehyde and butylideneaniline,reaction product of heptaldehyde and aniline, reaction product oftrichlotonylidenetetramine, condensate of a-ethyl-β-propylacrolein andaniline, and condensate of formaldehyde and alkylimidazole. (15)Guanidine compounds Diphenylguanidine, phenyltolylguanidine,phenylxylylguanidine, tolylxylylguanidine, di-o-tolylguanidine,o-tolylguanide, diphenylguanidine phthalate, tetramethylguanidine, anddi-o-tolylguanidine salt of dicatechol boric acid. (16) Thioureacompounds Thiocarboanilide, di-o-tolylthiourea, ethylenethiourea,diethylthiourea, dibutylthiourea, dilaurylthiourea, trimethylthiourea,dimethylethylthiourea, and tetramethylthiourea. (17) Thiazole compounds2-Mercaptobenzothiazole, dibenzothiazyl disulfide, cyclohexylamine saltof 2-mercaptobenzothiazole, 2-(2,4-dinitrophenylthio)benzothiazole, 2-(morpholinodithio)benzothiazole, 2- (2,6-dimethyl-4-morpholinothio)benzothiazole, N, N-diethylthiocarbamoyl-2-benzothiazolyldisulfide, 1,3-bis(2-benzothiazolylmercaptomethyl)urea,benzothiadiazylthio benzoate, 2-mercaptothiazoline, sodium salt of2-mercaptobenzothiazole, zinc salt of 2-mercaptobenzothiazole, andcomplex of dibenzothiazyl disulfide and zinc chloride. (18) Sulfenamidecompounds N-Cyclohexyl-2-benzothiazyl sulfenamide,N-tert-butyl-2-benzothiazyl sulfenamide, N-tert-oxtyl-2-benzothiazylsulfenamide, N-oxydiethylene-2- benzothiazyl sulfenamide,N,N-diethyl-2-benzothiazyl sulfenamide, N,N- diisopropyl-2-benzothiazylsulfenamide, and N,N-dicyclohexyl-2-benzothiazyl sulfenamide. (19)Thiuram compounds Tetramethylthiuram monosulfide, tetraethylthiurammonosulfide, tetrabutylthiuram monosulfide, dipentamethylenethiurammonosulfide, tetramethylthiuram disulfide, tetraethylthiuram disulfide,tetrabutylthiuram disulfide, N,N′-dimethyl-N,N′-diphenylthiuramdisulfide, N,N′-diethyl-N,N′- diphenylthiuram disulfide,dipentamethylenethiuram disulfide, dipentamethylenethiuram tetrasulfide,and cyclic thiuram. (20) Salts of dithiocarbamic acid Sodiumdimethyldithiocarbamate, sodium diethyldithiocarbamate, sodiumdibutyldithiocarbamate, sodium pentamethylenedithiocarbamate, sodiumcyclohexylethyldithiocarbamate, potassium dimethyldithiocarbamate, leaddimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincdiethyldithiocarbamate, zinc dibutyldithiocarbamate, zincdibenzyldithiocarbamate, zinc pentamethylenedithiocarbamate, zincdimethylpentamethylenedithiocarbamate, zinc ethylphenyldithiocarbamate,bismuth dimethyldithiocarbamate, cadmium diethyldithiocarbamate, cadmiumpentamethylenedithiocarbamate, selenium dimethyldithiocarbamate,selenium diethyldithiocarbamate, tellurium dimethyldithiocarbamate,tellurium diethyldithiocarbamate, iron dimethyldithiocarbamate, copperdimethyldithiocarbamate, diethylammonium diethyldithiocarbamate, N,N-dicyclohexylammonium dibutyldithiocarbamate, piperidiniumpentamethylenedithiocarbamate, cyclohexylethylammonium sodiumcyclohexylethyldithiocarbamate, pipecoliniummethylpentamethylenedithiocarbamate, and complex of zincpentamethylenedithiocarbamate and piperidine. (21) Salts of xanthogenicacid Sodium isopropylxanthate, zinc isopropylxanthate, zincbutylxanthate, and disulfide dibutylxanthate. (22) Acid phosphates Mono-and/or dimethyl phosphate, mono- and/or diethyl phosphate, mono- and/ordipropyl phosphate, mono- and/or dibutyl phosphate, mono- and/or dihexylphosphate, mono- and/or dioctyl phosphate, mono- and/or didecylphosphate, mono- and/or didodecyl phosphate, mono- and/or diphenylphosphate, mono- and/or dibenzyl phosphate, and mono- and/or didecanolphosphate.

[0052] The compounds recited above are examples of the polymerizationcatalysts for polymerization curing the composition for opticalmaterials comprising the compounds (a), (b), (c) and (d). The catalystis not limited thereto as far as the compound is effective for curingthe composition by polymerization. These catalysts may be used alone orin combination of two or more. The addition amount of the catalyst is0.0001 to 10.0parts by weight, preferably 0.0005 to 5.0 parts by weightbased on 100 parts by weight of the composition for optical materials.

[0053] Of the above compounds, preferred because of causing littlecoloring of the cured product are primary monoamines, secondarymonoamines, tertiary monoamines, tertiary polyamines, imidazolecompounds, amidine compounds, quaternary ammonium salts, phosphines,quaternary phosphonium salts, tertiary sulfonium salts, secondaryiodonium salts, and tin-containing Lewis acids. These catalysts may beused alone or in combination of two or more. Since depending on theingredients of the composition, the mixing ratio of the ingredients andthe curing method, the addition amount of the curing catalyst is notdetermined specifically, and usually 0.001 to 5.0 parts by weight,preferably 0.005 to 3.0 parts by weight, more preferably 0.01 to 1.0part by weight, and most preferably 0.01 to 0.5 part by weight. Ifexceeding 5.0 parts by weight, the resultant cured product is coloredand has a low refractive index and a poor heat resistance. If lower than0.001 part by weight, the composition is cured insufficiently to have apoor heat resistance.

[0054] To improve the dyeability of the polymerization-cured material ofthe composition of the present invention, a carboxylic acid, amercaptocarboxylic acid, a hydroxycarboxylic acid, an amide, a1,3-diketone, a 1,3-dicarboxylic acid, a 3-ketocarboxylic acid, an esterthereof or a compound having an unsaturated group may be combinedlyused. Examples thereof are described in Japanese Patent ApplicationLaid-Open No. 11-318960. These compounds may be used alone or incombination of two or more in an amount of 0.001 to 40 parts by weightbased on 100 parts by weight of the composition for optical materials.

[0055] In addition to the dyeability-improving compound mentioned above,the composition of the present invention may be cured in the presence ofa compound having two or more functional groups reactive with thestructure represented by Formula 1 in the compound (a); a compoundhaving one or more such functional groups and one or more otherhomopolymerizable functional groups; a compound having one or more suchhomopolymerizable functional groups; or a compound having onehomopolymerizable functional group which is also reactive with thestructure represented by Formula 1. Examples of the compound having twoor more functional groups reactive with the structure represented byFormula 1 in the compound (a) include epoxy compounds, known episulfidecompounds and anhydrides of polybasic carboxylic acids.

[0056] Examples of the compound having one or more functional groupsreactive with the structure represented by Formula 1 and one or moreother homopolymerizable functional groups include epoxy compounds,episulfide compounds and carboxylic acid anhydrides each having anunsaturated group such as methacryl group, acryl group, allyl group,vinyl group and aromatic vinyl group.

[0057] Examples of the compound having one or more homopolymerizablefunctional groups include compounds having an unsaturated group such asmethacryl group, acryl group, allyl group, vinyl group and aromaticvinyl group.

[0058] Examples of the compound having two or more functional groupsreactive with the structure represented by Formula 1 are described inJapanese Patent Application Laid-Open No. 11-318960.

[0059] Examples of the compound having two or more functional groupsreactive with the structure represented by Formula 1 in the compound (a)further include polyols described in Japanese Patent ApplicationLaid-Open No. 11- 166037.

[0060] The compound having two or more functional groups reactive withthe structure represented by Formula 1 in the compound (a), or thecompound having one or more such functional groups and one or more otherhomopolymerizable functional groups can be cured into a resin by thepolymerization with the composition of the present invention in thepresence of a curing catalyst. As the curing catalyst, the amines, thephosphines and the acids described above can be used.

[0061] If the compound having an unsaturated group is used, thepolymerization is preferably conducted in the presence of a radicalpolymerization initiator as the polymerization accelerator. Any compoundforming a radical by heating, ultraviolet light irradiation or electronbeams irradiation can be used as the radical polymerization initiator.Examples thereof are described in Japanese Patent Application Laid-OpenNo. 11-318960. The radical polymerization initiator may be used singlyor in combination of two or more.

[0062] Although the amount of the radical polymerization initiator to beused varies depending on the components of the composition and thecuring process and is not strictly limited, the amount is preferably0.01 to 5.0% by weight and more preferably 0.1 to 2.0% by weight basedon the total amount of the composition.

[0063] To improve the practical properties of the optical materialsbeing produced by polymerization-curing the composition of the presentinvention, the composition may be added with known additives such asantioxidants, ultraviolet light absorbents, anti-yellowing agents,bluing agents and pigments. When the composition of the presentinvention is easy to separate from molds during polymerization, it iseffective to use or add a known external and/or internal adhesionimprover, thereby controlling and improving the adhesion between thecured material being formed and the mold. On the other hand, when thecomposition of the present invention is difficult to release from moldsafter polymerization, it is effective to use or add a known external orinternal mold release agent, thereby improving the releasability of thecured material being formed from the molds.

[0064] In the present invention, the composition for optical materialcontaining the compounds (a), (b), (c) and (d) is uniformly mixed withthe curing catalyst and the additives such as the adhesion or moldrelease improver, antioxidants, ultraviolet absorbers, bluing agents,and property improving additives. The resultant uniform mixture is castinto a mold made of glass or metal, cured by polymerization underheating, and then released from the mold to obtain the optical material.

[0065] The production of the cured resin optical material of the presentinvention will be described in more detail. As described above, amixture of the main components and the optional components is cast intoa mold, and cured therein to the optical material. The main components,i.e., the compounds (a), (b), (c) and (d) may be purified, if desired,by distillation, recrystallization, column purification, washing,sublimation, etc. The compounds (a), (b), (c) and (d) as the maincomponents, and optionally, the compounds mentioned above, the curingcatalyst and the additives such as adhesion or mold release improver,antioxidants, ultraviolet absorbers and bluing agents may be all orpartly pre- reacted or pre-blended prior to casting into a mold in thepresence or absence of a catalyst with or without stirring, and thenmade into a composition to be cast into a mold. The components may bereacted or blended by adding each component stepwise. Alternatively, afew of the components are reacted or blended in separate containers andthen blended together in a single container. The order of the reactionor blend is not particularly limited.

[0066] The pre-blending or pre-reaction referred to herein includes amethod in which the compound (a) and the compound (b) are pre-blended orpre-reacted, and thereafter, the compound (c) and the compound (d) areseparately added or added after blending or reaction; a method in whichthe compound (b) and the compound (c) are pre-blended or pre-reacted,and thereafter, the compound (a) and the compound (d) are separatelyadded or added after blending or reaction; a method in which thecompound (a) and the compound (c) are pre-blended or pre-reacted, andthereafter, the compound (b) and the compound (d) are separately addedor added after blending or reaction; and a method in which the compound(a), the compound (b) and the compound (c) are pre-blended orpre-reacted, and thereafter, the compound (d) is added.

[0067] The reaction or blending temperature and time are not critical asfar as the components are sufficiently mixed. An excessively hightemperature and an excessively long period of time unfavorably make thecasting operation difficult because undesirable reaction between thestarting materials and additives is induced to increase the viscosity.The reaction or blending temperature is about −20 to 100° C., preferably−10 to 80° C., more preferably −5 to 70° C. The blending time is oneminute to 24 h, preferably five minutes to 10 h, and more preferably 10min to 8 h.

[0068] The degasification under reduced pressure prior to the mixing,during the mixing or after the mixing of the starting materials andadditives is preferred to prevent the generation of bubbles during thesubsequent casting step and curing step by polymerization. The degree ofevacuation is about 0.1 to 700 mmHg, preferably 10 to 300 mmHg. Toincrease the quality of the optical material of the invention, it ispreferred to remove impurities by filtering the composition beforecasting into a mold through a micro filter having a pore size of about0.1 to 5 pm.

[0069] The curing time is 0.1 to 200 h, preferably 1 to 100 h. Thecuring temperature is -10 to 160° C., preferably -10 to 140° C. Thepolymerization is carried out by keeping the starting mixture at a givenpolymerization temperature for a given period of time while raising thetemperature at 0.1 to 100° C./h, lowering the temperature at 0.1 to 100°C./h or using a combination thereof. After curing, it is preferred toanneal the optical material at 50 to 150° C. for 10 min to 5 h becausethe strain of the optical material can be removed. The optical materialmay be further subjected to surface treatment for improving dyeability,providing hard coating and impact resistance coating, and impartingnon-reflection or non-fogging properties.

[0070] The present invention will be described in more detail byreference to the following examples which should not be construed tolimit the scope of the invention thereto. The evaluation ofpolymerization products was carried out in the following manners.Refractive Index (nD):

[0071] Measured at 25° C. using Abbe refractometer. Impact Resistance:

[0072] Iron balls were dropped to a flat plate having a thickness of 2.5mm from the height of 127 cm while increasing the weight of the ballfrom 10 g with an increment of 10 g until the plate was broken. Theimpact resistance was expressed as the impact energy required to breakthe plate. Processability:

[0073] A flat plate of 2.5 mm thick was drilled to form a hole of 2 mmdiameter at a rotation speed of 2500 rpm and an insert speed of 600mm/min. The periphery of the hole was observed and the results wereevaluated by the following ratings.

[0074] Good: No chipping was observed at the periphery.

[0075] Poor: Chipping occurred at the periphery. EXAMPLE 1

[0076] With 100 parts by weight of mixture consisting of 59 parts byweight of bis(β-epithiopropyl) sulfide (compound (a)), 15 parts byweight of m-xylylene diisocyanate (compound (b)), 20 parts by weight ofbis(2-mercaptoethyl) sulfide (compound (c)) and 6 parts by weight ofsulfur (compound (d)), 0.1 part by weight of tetrabromophosphoniumbromide (catalyst), 0.1 part by weight of 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole (ultraviolet absorber) and0.1 part by weight of 2,6-di-tert-butyl-4-methylphenol were blendedunder stirring at room temperature to obtain a uniform liquid. Theresultant composition was cast into a mold for lens and cured bypolymerization in an oven by raising the temperature from 10° C. to 120°C. over 22 h to prepare a lens. The obtained lens had a high impactresistance, and showed excellent tone, dyeability, heat resistance andoxidation resistance. The lens was also excellent in optical propertiesand physical properties, and showed an excellent surface condition withlittle striae or surface deformation. The properties of the preparedlens are shown in Table 1. EXAMPLE 2

[0077] A mixture of 15 parts by weight of1,3-bis(isocyanatomethyl)cyclohexane (compound (b)), 19 parts by weightof 2,5-bis(isocyanatomethyl)-1,4-dithiane (compound (c)) and 0.03 partby weight of di-n-butyltin diacetate was subjected to pre-reaction at60° C. for 5 h. After adding 63 parts by weight of bis(β- epithiopropyl)sulfide (compound (a)), 6 parts by weight of sulfur (compound (d)) tothe resultant product, 0.1 part by weight of tetrabromophosphoniumbromide (catalyst), 0.1 part by weight of 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole (ultraviolet absorber) and 0.1 part by weightof 2,6- di-tert-butyl-4-methylphenol were blended under stirring at roomtemperature to obtain a uniform liquid. The resultant composition wascast into a mold for lens and cured by polymerization in an oven byraising the temperature from 10° C. to 120° C. over 22 h to prepare alens. The obtained lens had a high impact resistance, and showedexcellent tone, dyeability, heat resistance and oxidation resistance.The lens was also excellent in optical properties and physicalproperties, and showed an excellent surface condition with little striaeor surface deformation. The properties of the prepared lens are shown inTable 1. EXAMPLES 3-20

[0078] The polymerization curing procedure of Example 2 was repeatedexcept for changing the chemical composition and the catalyst as shownin Table 1. The pre-reaction of the compound (b) and the compound (c)was carried out in the presence of di-n-butyltin diacetate as thepre-reaction catalyst. In the examples where di-n-butyltin diacetate wasnot used, a pre-blend of he compound (b) and the compound (c) was used.In any of the examples, the obtained lens had a high impact resistance,and showed excellent tone, dyeability, heat resistance and oxidationresistance. The lens was also excellent in optical properties andphysical properties, and showed an excellent surface condition withlittle striae or surface deformation. The properties of the preparedlens are shown in Table 1. COMPARATIVE EXAMPLE 1

[0079] The procedure of Example 1 was repeated except for using 100parts by weight of bis(β-epithiopropyl) sulfide (compound (a)). Theresults are shown in Table 2. The impact resistance was poor because thecompounds (b), (c) and (d) were not used. COMPARATIVE EXAMPLE 2

[0080] The procedure of Example 1 was repeated except for using 70 partsby weight of bis(β-epithiopropyl) sulfide (compound (a)) and 30 parts byweight of m-xylylene diusocyanate (compound (b)). The results are shownin Table 2. The impact resistance was low because the compounds (c) and(d) were not used. COMPARATIVE EXAMPLE 3

[0081] The procedure of Example 1 was repeated except for using 70 partsby weight of bis(β-epithiopropyl) sulfide (compound (a)) and 30 parts byweight of bis(2-mercaptoethyl) sulfide (compound (c)). The results areshown in Table 2. The heat resistance was poor because the compounds (b)and (d) were not used. COMPARATIVE EXAMPLE 4

[0082] The procedure of Example 1 was repeated except for using 90 partsby weight of bis(β-epithiopropyl) sulfide (compound (a)) and 10 parts byweight of sulfur (compound (d)). The results are shown in Table 2. Theimpact resistance was poor because the compounds (b) and (c) were notused. COMPARATIVE EXAMPLE 5

[0083] The procedure of Example 1 was repeated except for using 52 partsby weight of m-xylylene diisocyanate (compound (b)) and 48 parts byweight of 1,3-bis[(2-mercaptoethyl)thio]-3-mercaptopropane. The resultsare shown in Table 2. The refractive index and Abbe's number were lowbecause the compounds (a) and (d) were not used. COMPARATIVE EXAMPLE 6

[0084] The procedure of Example 1 was repeated except for using 20 partsby weight of bis(β-epithiopropyl) sulfide (compound (a)), 38 parts byweight of m- xylylene diisocyanate (compound (b)) and 42 parts by weightof bis(2- mercaptoethyl) sulfide (compound (c)). The results are shownin Table 2. The refractive index was low because the compound (d) wasnot used. COMPARATIVE EXAMPLE 7

[0085] The procedure of Example 1 was repeated except for using 49 partsby weight of m-xylylene diisocyanate (compound (b)), 46 parts by weightof 1,2- bis[(2-mercaptoethyl)thio]-3-mercaptopropane and 5 parts byweight of sulfur (compound (d)). The results are shown in Table 2. Therefractive index and Abbe's number were low because the compound (a) wasnot used. TABLE 1 Chemical Composition (by weight) Examples (a) (b) (c)(d) Catalyst 1 BES (59) XDI (15) DMMD (20) S (6) TBPB (0.1) 2 BES (63)BIC (11) DMMD (19) S (7) TBPB (0.1) BTA (0.03) 3 BES (43) BIND (21) DMMD(29) S (7) TBPB (0.1) BTA (0.05) 4 BES (50) BIND (10) DMMD (15) S (25)TBPB (0.1) BTA (0.05) 5 BES (70) NBDI (11) BMT (14) S (5) TBPB (0.1) BTA(0.03) 6 BES (66) XDIT (18) BMES (12) S (4) TBPB (0.1) 7 BES (63) BIC(12) BMES (1) S (7) TBPB (0.1) DMMD (17) BTA (0.03) 8 BES (64) XDI (11)BMES (19) Se (6) TBPB (0.1) 9 BES (63) XDI (15) PETP (15) SSe (7) TBPB(0.1) 10 BED (65) NBDI (13) BMT (17) S (5) TBPB (0.1) BTA (0.03) 11 BED(60) XDI (15) BMT (20) S (5) TBPB (0.1) 12 BED (60) XDI (10) BMT (15) S(15) TBPB (0.1) 13 BED (45) BIND (21) DMMD (29) S (5) TBPB (0.1) BTA(0.05) 14 BED (55) BIND (10) DMMD (20) S (15) TBPB (0.1) BTA (0.05) 15BED (55) XDI (20) PETP (20) S (5) TBPB (0.1) BTA (0.04) 16 BESe (60) BIC(15) BMT (20) S (5) TBPB (0.1) BTA (0.03) 17 BESe (45) BIND (21) DMMD(29) S (5) TBPB (0.1) BTA (0.05) 18 BESe (63) BIND (10) PETP (23) SPb(4) TBPB (0.1) BTA (0.03) 19 BESe (56) BIND (17) DMMD (23) CS2 (4) TBPB(0.1) BTA (0.03) 20 BDS (76) XDI (7) BMES (13) S (4) TBPB (0.1)Refractive Index/ Impact Abbe's Number Resistance Examples nD/υD (J)Processability 1 1.70/34 3.9 good 2 1.70/36 4.3 good 3 1.70/35 4.2 good4 1.75/31 3.5 good 5 1.70/36 3.2 good 6 1.72/32 3.5 good 7 1.70/36 4.5good 8 1.70/35 3.2 good 9 1.69/35 3.2 good 10 1.72/34 3.5 good 111.72/32 3.3 good 12 1.75/30 3.3 good 13 1.72/34 3.3 good 14 1.75/31 3.3good 15 1.69/34 3.4 good 16 1.71/34 3.4 good 17 1.72/34 3.5 good 181.70/35 3.2 good 19 1.72/34 3.3 good 20 1.74/31 3.5 good

[0086] TABLE 2 Com- parative Chemical Composition (by weight) Examples(a) (b) (c) (d) Catalyst 1 BES (100) TBPB (0.1) 2 BES (70) XDI (30) TBPB(0.1) 3 BES (70) BMES (30) TBPB (0.1) 4 BES (90) S (10) TBPB (0.1) 5 XDI(52) BMT (48) BTA (0.1) 6 BDS (20) XDI (38) DMMD (42) TBPB (0.1) BTA(0.05) 7 XDI (49) BMT (46) S (5) BTA (0.1) Com- Refractive Index/ Impactparative Abbe's Number Resistance Examples nD/υD (J) Processability 11.71/36 1.6 poor 2 1.68/34 2.6 poor 3 1.71/36 1.9 good 4 1.72/35 1.2poor 5 1.66/32 4.5 good 6 1.63/30 1.8 poor 7 1.67/32 3.6 good

[0087] Industrial Applicability

[0088] The optical material obtained by polymerization curing thecomposition of the present invention can provide an optical resin thatis balanced with a sufficiently high refractive index and a good Abbe'snumber with a high impact resistance which cannot be attained by usingthe known materials.

What is claimed is:
 1. A composition for optical materials, comprising:(a) a compound having in one molecule at least one structure representedby the following Formula 1:

wherein R¹ is a Cβ-₁₀ hydrocarbon group, each of R², R³ and R⁴ is aCl-lo hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5,and n is 0 to 5; (b) a compound having in one molecule at least oneisocyanate group and/or isothiocyanate group; (c) a compound having inone molecule at least one mercapto group; and (d) an inorganic compoundhaving sulfur atom and/or selenium atom.
 2. The composition for opticalmaterials according to claim 1, wherein the compound (a) is representedby the following Formula 2:

wherein Rl is a Cβ-₁₀ hydrocarbon group, each of R², R³ and R⁴ is aC₁₋₁₀ hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5,and n is 0 to
 5. 3. The composition for optical materials according toclaim 1, wherein the compound (a) is represented by Formula 1 wherein Yis S or Se, m is 1, and n is 0 to2.
 4. The composition for opticalmaterials according to claim 2, wherein the compound (a) is representedby Formula 2 wherein Y is S or Se, m is 1, and n is 0 to
 2. 5. Thecomposition for optical materials according to claim 1, wherein thecompound (c) has a sulfide linkage.
 6. The composition for opticalmaterials according to claim 2, wherein the compound (c) has a sulfidelinkage.
 7. The composition for optical materials according to claim 1,wherein the compound (d) is sulfur, carbon disulfide, selenium, leadselenide or selenium sulfide.
 8. The composition for optical materialsaccording to claim 2, wherein the compound (d) is sulfur, carbondisulfide, selenium, lead selenide or selenium sulfide.
 9. An opticalmaterial produced by polymerization curing the composition as defined inclaim
 1. 10. An optical material produced by polymerization curing thecomposition as defined in claim
 2. 11. An optical lens comprising theoptical material as defined in claim
 9. 12. An optical lens comprisingthe optical material as defined in claim
 10. 13. A method of producingan optical material, comprising a step of polymerization curing thecomposition as defined in claim
 1. 14. A method of producing an opticalmaterial, comprising a step of polymerization curing the composition asdefined in claim 2.